# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Michal Ksawery Cyranski' _publ_contact_author_email chamis@chem.uw.edu.pl loop_ _publ_author_name 'M. H. Jamroz' 'A. Rygula' 'L. Dobrzycki' 'M. K. Cyranski' J.Cz.Dobrowolski ; M.Baranska ; data_a1 _database_code_depnum_ccdc_archive 'CCDC 800713' #TrackingRef 'I.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 O4' _chemical_formula_weight 240.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.059(3) _cell_length_b 3.6850(4) _cell_length_c 21.004(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.424(15) _cell_angle_gamma 90.00 _cell_volume 1503.7(3) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1833 _cell_measurement_theta_min 2.9097 _cell_measurement_theta_max 28.0651 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; Crystal is twinned by reticular pseudomerohedry [n = 2, twin obliqiuty = 0.75(2) deg.] ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3570 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0989 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3570 _reflns_number_gt 1582 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3570 _refine_ls_number_parameters 279 _refine_ls_number_restraints 112 _refine_ls_R_factor_all 0.1336 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2013 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.880 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7945(4) 0.448(2) 0.1887(3) 0.046(2) Uani 0.611(5) 1 d P A 1 O2 O 0.7970(3) 0.7605(13) 0.3005(3) 0.057(2) Uani 0.611(5) 1 d P A 1 H2O H 0.8133 0.6709 0.2709 0.068 Uiso 0.611(5) 1 d PR A 1 O3 O 0.7288(3) 0.9952(15) 0.3867(2) 0.058(2) Uani 0.611(5) 1 d P A 1 H3O H 0.7710 0.9768 0.3888 0.069 Uiso 0.611(5) 1 d PR A 1 O4 O 0.5170(4) 0.5071(17) 0.1299(3) 0.053(2) Uani 0.611(5) 1 d P A 1 C1 C 0.6816(5) 0.0862(19) 0.0032(3) 0.0234(16) Uani 0.611(5) 1 d PDU A 1 H1 H 0.7033 -0.0101 -0.0285 0.028 Uiso 0.611(5) 1 calc PR A 1 C2 C 0.7229(5) 0.2025(18) 0.0641(3) 0.0263(19) Uani 0.611(5) 1 d PDU A 1 H2 H 0.7717 0.1974 0.0737 0.032 Uiso 0.611(5) 1 calc PR A 1 C3 C 0.6873(5) 0.3288(17) 0.1107(3) 0.0184(17) Uani 0.611(5) 1 d PDU A 1 C4 C 0.7292(5) 0.467(2) 0.1748(4) 0.0302(19) Uani 0.611(5) 1 d PU A 1 C5 C 0.6938(5) 0.6187(19) 0.2223(3) 0.021(2) Uani 0.611(5) 1 d PDU A 1 C6 C 0.7293(5) 0.753(2) 0.2828(4) 0.044(3) Uani 0.611(5) 1 d PDU A 1 C7 C 0.6929(5) 0.864(2) 0.3283(4) 0.030(2) Uani 0.611(5) 1 d PDU A 1 C8 C 0.6248(5) 0.874(2) 0.3113(4) 0.032(2) Uani 0.611(5) 1 d PDU A 1 H8 H 0.6003 0.9523 0.3421 0.038 Uiso 0.611(5) 1 calc PR A 1 C9 C 0.5900(5) 0.7725(19) 0.2499(4) 0.033(2) Uani 0.611(5) 1 d PDU A 1 H9 H 0.5416 0.8056 0.2376 0.039 Uiso 0.611(5) 1 calc PR A 1 C10 C 0.6205(5) 0.6265(19) 0.2050(4) 0.026(2) Uani 0.611(5) 1 d PDU A 1 C11 C 0.5788(6) 0.489(2) 0.1421(4) 0.028(2) Uani 0.611(5) 1 d PU A 1 C12 C 0.6155(5) 0.348(2) 0.0971(3) 0.0263(19) Uani 0.611(5) 1 d PDU A 1 C13 C 0.5735(6) 0.2428(19) 0.0337(3) 0.039(2) Uani 0.611(5) 1 d PDU A 1 H13 H 0.5248 0.2629 0.0232 0.047 Uiso 0.611(5) 1 calc PR A 1 C14 C 0.6085(4) 0.108(2) -0.0124(4) 0.033(2) Uani 0.611(5) 1 d PDU A 1 H14 H 0.5827 0.0307 -0.0544 0.040 Uiso 0.611(5) 1 calc PR A 1 O1B O 0.5378(2) 0.5108(16) 0.1316(2) 0.035(4) Uiso 0.389(5) 1 d PG A 2 O2B O 0.5421(2) 0.7568(15) 0.2488(2) 0.063(4) Uiso 0.389(5) 1 d PG A 2 H2OB H 0.5238 0.6805 0.2108 0.076 Uiso 0.389(5) 1 d PG A 2 O3B O 0.6162(3) 1.0152(15) 0.3636(2) 0.058(3) Uiso 0.389(5) 1 d PG A 2 H3OB H 0.5736 0.9972 0.3475 0.069 Uiso 0.389(5) 1 d PG A 2 O4B O 0.8157(2) 0.484(2) 0.1973(3) 0.052(6) Uiso 0.389(5) 1 d PG A 2 C1B C 0.6413(4) 0.0971(17) -0.0039(2) 0.010(3) Uiso 0.389(5) 1 d PG A 2 H1B H 0.6175 0.0118 -0.0462 0.012 Uiso 0.389(5) 1 d PG A 2 C2B C 0.6031(3) 0.2307(16) 0.0387(2) 0.026(4) Uiso 0.389(5) 1 d PG A 2 H2B H 0.5542 0.2284 0.0273 0.032 Uiso 0.389(5) 1 d PG A 2 C3B C 0.6418(3) 0.3698(12) 0.10013(18) 0.012(3) Uiso 0.389(5) 1 d PG A 2 C4B C 0.6032(2) 0.5012(11) 0.14767(18) 0.030(5) Uiso 0.389(5) 1 d PG A 2 C5B C 0.6420(2) 0.6262(10) 0.21292(17) 0.015(3) Uiso 0.389(5) 1 d PGU A 2 C6B C 0.6097(2) 0.7510(11) 0.25952(18) 0.024(4) Uiso 0.389(5) 1 d PGU A 2 C7B C 0.6486(2) 0.8971(12) 0.31880(19) 0.012(3) Uiso 0.389(5) 1 d PGU A 2 C8B C 0.7170(2) 0.8829(16) 0.3326(2) 0.011(3) Uiso 0.389(5) 1 d PGU A 2 H8B H 0.7436 0.9790 0.3729 0.014 Uiso 0.389(5) 1 d PG A 2 C9B C 0.7487(2) 0.7303(17) 0.2889(2) 0.014(3) Uiso 0.389(5) 1 d PGU A 2 H9B H 0.7973 0.7016 0.3020 0.017 Uiso 0.389(5) 1 d PG A 2 C10B C 0.7153(2) 0.6172(13) 0.2281(2) 0.022(5) Uiso 0.389(5) 1 d PG A 2 C11B C 0.7537(2) 0.4897(15) 0.1814(2) 0.023(4) Uiso 0.389(5) 1 d PG A 2 C12B C 0.7138(3) 0.3666(13) 0.1187(2) 0.017(4) Uiso 0.389(5) 1 d PG A 2 C13B C 0.7527(3) 0.2158(17) 0.0760(3) 0.039(4) Uiso 0.389(5) 1 d PG A 2 H13B H 0.8015 0.2040 0.0887 0.047 Uiso 0.389(5) 1 d PG A 2 C14B C 0.7145(4) 0.0854(17) 0.0140(2) 0.034(4) Uiso 0.389(5) 1 d PG A 2 H14B H 0.7383 -0.0115 -0.0160 0.041 Uiso 0.389(5) 1 d PG A 2 C24 C 0.9259(3) 0.4880(13) -0.0222(3) 0.0471(15) Uani 1 1 d . . . C25 C 0.9605(3) 0.6234(13) 0.0429(2) 0.0430(14) Uani 1 1 d . . . C26 C 0.9243(3) 0.7433(12) 0.0856(3) 0.0481(17) Uani 1 1 d D . . H26 H 0.8754 0.7395 0.0720 0.058 Uiso 0.50 1 calc PR . . C27 C 0.9556(4) 0.8705(15) 0.1478(3) 0.0559(16) Uani 1 1 d DU . . H27 H 0.9276 0.9519 0.1754 0.067 Uiso 0.50 1 calc PR . . C28 C 1.0239(3) 0.8826(15) 0.1704(3) 0.0541(16) Uani 1 1 d . . . H28 H 1.0445 0.9709 0.2133 0.065 Uiso 1 1 calc R . . C29 C 1.0640(4) 0.7622(11) 0.1293(2) 0.0534(18) Uani 1 1 d . . . H29 H 1.1128 0.7643 0.1440 0.064 Uiso 1 1 calc R . . C30 C 1.0314(3) 0.6364(13) 0.0653(2) 0.0425(14) Uani 1 1 d . . . O21 O 0.8621(2) 0.4818(11) -0.04146(15) 0.0665(12) Uani 1 1 d . . . O22 O 0.8592(3) 0.7456(16) 0.0665(3) 0.050(2) Uani 0.50 1 d PD . . H22 H 0.8470 0.6618 0.0281 0.060 Uiso 0.50 1 d PR . . O23 O 0.9225(3) 0.972(2) 0.1894(3) 0.076(2) Uani 0.50 1 d PD . . H23 H 0.8800 0.9599 0.1722 0.091 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.026(3) 0.065(5) 0.049(4) 0.011(3) 0.015(3) 0.008(3) O2 0.070(5) 0.062(5) 0.035(3) 0.001(3) 0.006(3) 0.000(3) O3 0.084(4) 0.048(4) 0.041(4) 0.007(3) 0.016(3) 0.006(4) O4 0.040(4) 0.059(5) 0.067(5) -0.010(4) 0.026(3) -0.018(4) C1 0.023(2) 0.025(2) 0.025(2) -0.0007(17) 0.0107(18) 0.0050(18) C2 0.028(3) 0.019(3) 0.034(3) 0.009(3) 0.012(3) 0.007(3) C3 0.024(4) 0.005(3) 0.026(3) 0.000(2) 0.005(2) -0.002(3) C4 0.028(3) 0.024(3) 0.043(4) 0.018(3) 0.016(3) 0.001(3) C5 0.032(3) 0.011(3) 0.022(3) 0.004(2) 0.009(2) 0.004(3) C6 0.043(3) 0.042(3) 0.046(3) 0.0054(19) 0.0111(19) 0.0047(19) C7 0.039(4) 0.028(3) 0.024(3) 0.003(3) 0.011(3) -0.002(3) C8 0.037(4) 0.025(3) 0.038(4) 0.001(3) 0.019(3) -0.001(3) C9 0.032(4) 0.029(4) 0.040(3) 0.008(3) 0.016(3) -0.003(3) C10 0.029(3) 0.015(3) 0.037(4) 0.006(3) 0.013(3) 0.002(3) C11 0.024(3) 0.026(4) 0.033(4) 0.003(3) 0.007(3) -0.004(3) C12 0.025(3) 0.019(3) 0.037(4) 0.004(3) 0.011(3) -0.013(3) C13 0.051(4) 0.029(4) 0.035(3) -0.007(3) 0.007(3) -0.008(3) C14 0.034(3) 0.025(3) 0.041(3) 0.004(3) 0.012(3) 0.002(3) C24 0.066(4) 0.022(3) 0.038(3) 0.004(3) -0.015(3) 0.010(3) C25 0.074(4) 0.019(3) 0.031(3) 0.002(2) 0.004(3) 0.010(3) C26 0.059(4) 0.031(4) 0.045(3) 0.013(3) -0.005(3) -0.003(3) C27 0.099(5) 0.033(3) 0.039(3) -0.002(3) 0.024(3) 0.000(3) C28 0.081(4) 0.036(3) 0.035(3) 0.014(3) -0.005(3) -0.001(3) C29 0.121(5) 0.011(3) 0.030(3) 0.001(2) 0.020(3) -0.002(3) C30 0.072(4) 0.018(3) 0.032(3) 0.010(2) 0.004(3) 0.007(3) O21 0.077(3) 0.063(3) 0.044(2) -0.001(2) -0.013(2) 0.009(2) O22 0.053(5) 0.064(6) 0.031(4) -0.012(3) 0.003(4) -0.007(3) O23 0.065(5) 0.116(7) 0.045(4) -0.007(5) 0.014(4) 0.008(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.272(11) . ? O2 C6 1.316(11) . ? O2 H2O 0.8400 . ? O3 C7 1.349(8) . ? O3 H3O 0.8400 . ? O4 C11 1.203(12) . ? C1 C2 1.406(8) . ? C1 C14 1.423(11) . ? C1 H1 0.9500 . ? C2 C3 1.427(8) . ? C2 H2 0.9500 . ? C3 C12 1.398(12) . ? C3 C4 1.487(10) . ? C4 C5 1.472(10) . ? C5 C6 1.384(8) . ? C5 C10 1.424(12) . ? C6 C7 1.399(9) . ? C7 C8 1.324(12) . ? C8 C9 1.357(8) . ? C8 H8 0.9500 . ? C9 C10 1.356(8) . ? C9 H9 0.9500 . ? C10 C11 1.466(10) . ? C11 C12 1.433(10) . ? C12 C13 1.439(8) . ? C13 C14 1.420(8) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? O1B C4B 1.2718 . ? O2B C6B 1.3169 . ? O2B H2OB 0.8400 . ? O3B C7B 1.3418 . ? O3B H3OB 0.8400 . ? O4B C11B 1.2039 . ? C1B C2B 1.4052 . ? C1B C14B 1.4231 . ? C1B H1B 0.9500 . ? C2B C3B 1.4252 . ? C2B H2B 0.9500 . ? C3B C12B 1.3993 . ? C3B C4B 1.4886 . ? C4B C5B 1.4711 . ? C5B C6B 1.3809 . ? C5B C10B 1.4250 . ? C6B C7B 1.4024 . ? C7B C8B 1.3297 . ? C8B C9B 1.3619 . ? C8B H8B 0.9500 . ? C9B C10B 1.3529 . ? C9B H9B 0.9500 . ? C10B C11B 1.4666 . ? C11B C12B 1.4350 . ? C12B C13B 1.4372 . ? C13B C14B 1.4200 . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C24 O21 1.244(5) . ? C24 C25 1.459(6) . ? C24 C30 1.466(7) 3_765 ? C25 C26 1.360(7) . ? C25 C30 1.383(7) . ? C26 C27 1.384(7) . ? C26 H26 0.9500 . ? C27 C28 1.333(8) . ? C27 H27 0.9500 . ? C28 C29 1.391(7) . ? C28 H28 0.9500 . ? C29 C30 1.418(7) . ? C29 H29 0.9500 . ? C30 C24 1.466(7) 3_765 ? O22 H22 0.8400 . ? O23 H23 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 H2O 110.3 . . ? C7 O3 H3O 108.6 . . ? C2 C1 C14 122.1(6) . . ? C2 C1 H1 118.9 . . ? C14 C1 H1 118.9 . . ? C1 C2 C3 116.2(7) . . ? C1 C2 H2 121.9 . . ? C3 C2 H2 121.9 . . ? C12 C3 C2 122.8(7) . . ? C12 C3 C4 119.4(6) . . ? C2 C3 C4 117.7(7) . . ? O1 C4 C5 120.5(8) . . ? O1 C4 C3 120.5(7) . . ? C5 C4 C3 118.9(8) . . ? C6 C5 C10 119.4(8) . . ? C6 C5 C4 122.3(9) . . ? C10 C5 C4 118.4(7) . . ? O2 C6 C5 121.7(8) . . ? O2 C6 C7 118.5(8) . . ? C5 C6 C7 119.6(9) . . ? C8 C7 O3 121.0(7) . . ? C8 C7 C6 120.2(8) . . ? O3 C7 C6 118.4(8) . . ? C7 C8 C9 120.0(8) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 123.8(9) . . ? C10 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? C9 C10 C5 116.4(8) . . ? C9 C10 C11 120.6(9) . . ? C5 C10 C11 123.0(7) . . ? O4 C11 C12 123.4(8) . . ? O4 C11 C10 119.9(8) . . ? C12 C11 C10 116.6(8) . . ? C3 C12 C11 123.7(7) . . ? C3 C12 C13 120.8(7) . . ? C11 C12 C13 115.4(8) . . ? C14 C13 C12 116.7(9) . . ? C14 C13 H13 121.6 . . ? C12 C13 H13 121.6 . . ? C13 C14 C1 121.3(8) . . ? C13 C14 H14 119.4 . . ? C1 C14 H14 119.4 . . ? C6B O2B H2OB 110.1 . . ? C7B O3B H3OB 108.4 . . ? C2B C1B C14B 122.1 . . ? C2B C1B H1B 118.9 . . ? C14B C1B H1B 118.9 . . ? C1B C2B C3B 116.2 . . ? C1B C2B H2B 121.9 . . ? C3B C2B H2B 121.9 . . ? C12B C3B C2B 122.8 . . ? C12B C3B C4B 119.3 . . ? C2B C3B C4B 117.8 . . ? O1B C4B C5B 120.6 . . ? O1B C4B C3B 120.4 . . ? C5B C4B C3B 119.0 . . ? C6B C5B C10B 119.4 . . ? C6B C5B C4B 122.1 . . ? C10B C5B C4B 118.5 . . ? O2B C6B C5B 122.0 . . ? O2B C6B C7B 117.9 . . ? C5B C6B C7B 120.0 . . ? C8B C7B O3B 120.8 . . ? C8B C7B C6B 119.7 . . ? O3B C7B C6B 119.1 . . ? C7B C8B C9B 119.9 . . ? C7B C8B H8B 120.1 . . ? C9B C8B H8B 120.1 . . ? C10B C9B C8B 124.0 . . ? C10B C9B H9B 118.0 . . ? C8B C9B H9B 118.0 . . ? C9B C10B C5B 116.4 . . ? C9B C10B C11B 120.7 . . ? C5B C10B C11B 122.9 . . ? O4B C11B C12B 123.4 . . ? O4B C11B C10B 119.9 . . ? C12B C11B C10B 116.7 . . ? C3B C12B C11B 123.6 . . ? C3B C12B C13B 120.8 . . ? C11B C12B C13B 115.5 . . ? C14B C13B C12B 116.7 . . ? C14B C13B H13B 121.6 . . ? C12B C13B H13B 121.6 . . ? C13B C14B C1B 121.2 . . ? C13B C14B H14B 119.4 . . ? C1B C14B H14B 119.4 . . ? O21 C24 C25 121.4(6) . . ? O21 C24 C30 120.4(5) . 3_765 ? C25 C24 C30 118.2(5) . 3_765 ? C26 C25 C30 116.0(5) . . ? C26 C25 C24 121.4(6) . . ? C30 C25 C24 122.6(5) . . ? C25 C26 C27 122.7(6) . . ? C25 C26 H26 118.6 . . ? C27 C26 H26 118.6 . . ? C28 C27 C26 122.1(6) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C27 C28 C29 118.1(6) . . ? C27 C28 H28 121.0 . . ? C29 C28 H28 121.0 . . ? C28 C29 C30 119.4(7) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C25 C30 C29 121.7(6) . . ? C25 C30 C24 119.2(5) . 3_765 ? C29 C30 C24 119.1(6) . 3_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 2.8(9) . . . . ? C1 C2 C3 C12 -1.7(9) . . . . ? C1 C2 C3 C4 -177.8(6) . . . . ? C12 C3 C4 O1 179.1(7) . . . . ? C2 C3 C4 O1 -4.8(9) . . . . ? C12 C3 C4 C5 0.3(9) . . . . ? C2 C3 C4 C5 176.5(6) . . . . ? O1 C4 C5 C6 1.4(10) . . . . ? C3 C4 C5 C6 -179.8(6) . . . . ? O1 C4 C5 C10 -178.7(7) . . . . ? C3 C4 C5 C10 0.0(9) . . . . ? C10 C5 C6 O2 -178.3(7) . . . . ? C4 C5 C6 O2 1.5(11) . . . . ? C10 C5 C6 C7 5.8(11) . . . . ? C4 C5 C6 C7 -174.3(7) . . . . ? O2 C6 C7 C8 177.3(8) . . . . ? C5 C6 C7 C8 -6.7(12) . . . . ? O2 C6 C7 O3 4.3(10) . . . . ? C5 C6 C7 O3 -179.8(7) . . . . ? O3 C7 C8 C9 173.7(7) . . . . ? C6 C7 C8 C9 0.8(12) . . . . ? C7 C8 C9 C10 6.3(12) . . . . ? C8 C9 C10 C5 -6.8(11) . . . . ? C8 C9 C10 C11 173.7(7) . . . . ? C6 C5 C10 C9 0.7(11) . . . . ? C4 C5 C10 C9 -179.2(6) . . . . ? C6 C5 C10 C11 -179.9(6) . . . . ? C4 C5 C10 C11 0.2(11) . . . . ? C9 C10 C11 O4 0.3(11) . . . . ? C5 C10 C11 O4 -179.1(7) . . . . ? C9 C10 C11 C12 178.6(7) . . . . ? C5 C10 C11 C12 -0.9(10) . . . . ? C2 C3 C12 C11 -177.0(6) . . . . ? C4 C3 C12 C11 -1.0(10) . . . . ? C2 C3 C12 C13 -0.9(10) . . . . ? C4 C3 C12 C13 175.1(6) . . . . ? O4 C11 C12 C3 179.5(7) . . . . ? C10 C11 C12 C3 1.3(10) . . . . ? O4 C11 C12 C13 3.2(10) . . . . ? C10 C11 C12 C13 -175.0(6) . . . . ? C3 C12 C13 C14 2.4(10) . . . . ? C11 C12 C13 C14 178.8(6) . . . . ? C12 C13 C14 C1 -1.4(10) . . . . ? C2 C1 C14 C13 -1.3(10) . . . . ? C14B C1B C2B C3B 2.8 . . . . ? C1B C2B C3B C12B -1.8 . . . . ? C1B C2B C3B C4B -177.8 . . . . ? C12B C3B C4B O1B 179.1 . . . . ? C2B C3B C4B O1B -4.8 . . . . ? C12B C3B C4B C5B 0.3 . . . . ? C2B C3B C4B C5B 176.4 . . . . ? O1B C4B C5B C6B 1.3 . . . . ? C3B C4B C5B C6B -179.9 . . . . ? O1B C4B C5B C10B -178.7 . . . . ? C3B C4B C5B C10B 0.1 . . . . ? C10B C5B C6B O2B -178.3 . . . . ? C4B C5B C6B O2B 1.7 . . . . ? C10B C5B C6B C7B 5.6 . . . . ? C4B C5B C6B C7B -174.4 . . . . ? O2B C6B C7B C8B 177.3 . . . . ? C5B C6B C7B C8B -6.5 . . . . ? O2B C6B C7B O3B 4.1 . . . . ? C5B C6B C7B O3B -179.7 . . . . ? O3B C7B C8B C9B 173.8 . . . . ? C6B C7B C8B C9B 0.7 . . . . ? C7B C8B C9B C10B 6.3 . . . . ? C8B C9B C10B C5B -6.9 . . . . ? C8B C9B C10B C11B 173.7 . . . . ? C6B C5B C10B C9B 0.8 . . . . ? C4B C5B C10B C9B -179.2 . . . . ? C6B C5B C10B C11B -179.8 . . . . ? C4B C5B C10B C11B 0.2 . . . . ? C9B C10B C11B O4B 0.2 . . . . ? C5B C10B C11B O4B -179.1 . . . . ? C9B C10B C11B C12B 178.5 . . . . ? C5B C10B C11B C12B -0.8 . . . . ? C2B C3B C12B C11B -177.0 . . . . ? C4B C3B C12B C11B -1.1 . . . . ? C2B C3B C12B C13B -0.7 . . . . ? C4B C3B C12B C13B 175.2 . . . . ? O4B C11B C12B C3B 179.5 . . . . ? C10B C11B C12B C3B 1.3 . . . . ? O4B C11B C12B C13B 3.1 . . . . ? C10B C11B C12B C13B -175.1 . . . . ? C3B C12B C13B C14B 2.3 . . . . ? C11B C12B C13B C14B 178.9 . . . . ? C12B C13B C14B C1B -1.4 . . . . ? C2B C1B C14B C13B -1.2 . . . . ? O21 C24 C25 C26 1.0(8) . . . . ? C30 C24 C25 C26 180.0(5) 3_765 . . . ? O21 C24 C25 C30 -179.4(5) . . . . ? C30 C24 C25 C30 -0.4(8) 3_765 . . . ? C30 C25 C26 C27 -0.2(7) . . . . ? C24 C25 C26 C27 179.5(5) . . . . ? C25 C26 C27 C28 -0.3(8) . . . . ? C26 C27 C28 C29 0.0(8) . . . . ? C27 C28 C29 C30 0.8(7) . . . . ? C26 C25 C30 C29 0.9(7) . . . . ? C24 C25 C30 C29 -178.7(4) . . . . ? C26 C25 C30 C24 -180.0(4) . . . 3_765 ? C24 C25 C30 C24 0.4(8) . . . 3_765 ? C28 C29 C30 C25 -1.3(7) . . . . ? C28 C29 C30 C24 179.6(4) . . . 3_765 ? C25 C24 O21 O21 -12.3(4) . . . 4_576 ? C30 C24 O21 O21 168.7(4) 3_765 . . 4_576 ? C25 C24 O21 O21 157.0(4) . . . 1_554 ? C30 C24 O21 O21 -22.0(4) 3_765 . . 1_554 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.84 1.86 2.605(8) 146.5 . O3 H3O O21 0.84 2.04 2.724(7) 137.8 4_576 O3 H3O O2 0.84 2.20 2.671(8) 115.7 . O2B H2OB O1B 0.84 1.86 2.605 146.5 . O3B H3OB O2B 0.84 2.20 2.672 115.7 . O3B H3OB O1B 0.84 2.38 3.117(8) 146.4 2_655 O22 H22 O21 0.84 1.70 2.480(7) 153.6 . O23 H23 O22 0.84 2.30 2.710(9) 110.7 . O23 H23 O4B 0.84 2.31 2.834(10) 120.5 . O23 H23 O1 0.84 2.57 3.107(9) 123.0 1_565 O3B H3OB O4 0.84 1.99 2.710(10) 143.3 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.481 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.067 # Attachment 'II.CIF' data_aliz _database_code_depnum_ccdc_archive 'CCDC 800714' #TrackingRef 'II.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 O4' _chemical_formula_weight 240.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.1319(4) _cell_length_b 3.7102(2) _cell_length_c 16.8711(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.455(5) _cell_angle_gamma 90.00 _cell_volume 500.57(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3856 _cell_measurement_theta_min 5.3280 _cell_measurement_theta_max 66.9898 _exptl_crystal_description Planar _exptl_crystal_colour Orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8576 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; Crystal is twinned by reticular pseudomerohedry [n = 2, twin obliqiuty = 2.135(4) deg.] ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 10.3347 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1781 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0832 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.33 _diffrn_reflns_theta_max 67.10 _reflns_number_total 1781 _reflns_number_gt 1329 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3.1' _computing_publication_material SHELXTL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1781 _refine_ls_number_parameters 191 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1877(8) 0.6680(16) 0.3288(4) 0.048(2) Uani 0.771(4) 1 d P A 1 H1 H -0.2981 0.7596 0.3142 0.058 Uiso 0.771(4) 1 calc PR A 1 C2 C -0.1320(7) 0.5305(14) 0.4051(3) 0.0356(15) Uani 0.771(4) 1 d P A 1 H2 H -0.2046 0.5220 0.4433 0.043 Uiso 0.771(4) 1 calc PR A 1 C3 C 0.0344(7) 0.4024(13) 0.4259(3) 0.0293(13) Uani 0.771(4) 1 d P A 1 C4 C 0.0861(7) 0.2492(13) 0.5076(3) 0.0309(12) Uani 0.771(4) 1 d P A 1 C5 C 0.2591(5) 0.1188(11) 0.5290(3) 0.0238(10) Uani 0.771(4) 1 d P A 1 C6 C 0.3150(6) -0.0185(13) 0.6069(2) 0.0288(11) Uani 0.771(4) 1 d P A 1 C7 C 0.4813(6) -0.1354(12) 0.6299(3) 0.0271(10) Uani 0.771(4) 1 d P A 1 C8 C 0.5874(6) -0.1250(12) 0.5743(3) 0.0297(10) Uani 0.771(4) 1 d P A 1 H8 H 0.6997 -0.2054 0.5892 0.036 Uiso 0.771(4) 1 calc PR A 1 C9 C 0.5306(6) 0.0014(11) 0.4976(3) 0.0294(12) Uani 0.771(4) 1 d P A 1 H9 H 0.6045 0.0022 0.4599 0.035 Uiso 0.771(4) 1 calc PR A 1 C10 C 0.3691(5) 0.1275(10) 0.4736(2) 0.0254(10) Uani 0.771(4) 1 d P A 1 C11 C 0.3136(7) 0.2651(12) 0.3918(3) 0.0298(13) Uani 0.771(4) 1 d P A 1 C12 C 0.1409(7) 0.4088(13) 0.3704(3) 0.0268(12) Uani 0.771(4) 1 d P A 1 C13 C 0.0825(8) 0.5470(17) 0.2941(3) 0.0363(17) Uani 0.771(4) 1 d P A 1 H13 H 0.1546 0.5571 0.2557 0.044 Uiso 0.771(4) 1 calc PR A 1 C14 C -0.0801(9) 0.6702(17) 0.2738(3) 0.045(2) Uani 0.771(4) 1 d P A 1 H14 H -0.1191 0.7585 0.2209 0.053 Uiso 0.771(4) 1 calc PR A 1 O1 O -0.0117(4) 0.2387(12) 0.5564(2) 0.0410(10) Uani 0.771(4) 1 d P A 1 O2 O 0.2159(3) -0.0371(8) 0.66265(16) 0.0398(7) Uani 0.771(4) 1 d P A 1 H2O H 0.1182 0.0243 0.6418 0.060 Uiso 0.771(4) 1 calc PR A 1 O3 O 0.5346(4) -0.2610(8) 0.70480(15) 0.0394(7) Uani 0.771(4) 1 d P A 1 H3O H 0.4573 -0.2428 0.7316 0.059 Uiso 0.771(4) 1 calc PR A 1 O4 O 0.4075(5) 0.2672(10) 0.3427(2) 0.0420(12) Uani 0.771(4) 1 d P A 1 C1B C -0.0995(11) 0.614(4) 0.2744(6) 0.026(6) Uiso 0.229(4) 1 d PG A 2 H1B H -0.1359 0.6878 0.2202 0.031 Uiso 0.229(4) 1 d PG A 2 C2B C 0.0622(10) 0.492(3) 0.2999(5) 0.029(7) Uiso 0.229(4) 1 d PG A 2 H2B H 0.1388 0.4859 0.2636 0.034 Uiso 0.229(4) 1 d PG A 2 C3B C 0.1125(8) 0.376(2) 0.3806(4) 0.020(5) Uiso 0.229(4) 1 d PGU A 2 C4B C 0.2882(7) 0.257(2) 0.4053(3) 0.022(6) Uiso 0.229(4) 1 d PG A 2 C5B C 0.3394(6) 0.1347(15) 0.4890(3) 0.018(4) Uiso 0.229(4) 1 d PGU A 2 C6B C 0.5036(6) 0.0093(14) 0.5142(3) 0.027(6) Uiso 0.229(4) 1 d PG A 2 C7B C 0.5548(7) -0.1194(16) 0.5933(3) 0.018(4) Uiso 0.229(4) 1 d PGU A 2 C8B C 0.4437(8) -0.110(2) 0.6465(3) 0.034(7) Uiso 0.229(4) 1 d PG A 2 H8B H 0.4775 -0.1944 0.7002 0.041 Uiso 0.229(4) 1 d PG A 2 C9B C 0.2844(8) 0.022(3) 0.6219(3) 0.017(4) Uiso 0.229(4) 1 d PGU A 2 H9B H 0.2106 0.0307 0.6595 0.020 Uiso 0.229(4) 1 d PG A 2 C10B C 0.2286(7) 0.141(2) 0.5440(4) 0.019(4) Uiso 0.229(4) 1 d PGU A 2 C11B C 0.0575(7) 0.275(3) 0.5196(5) 0.018(5) Uiso 0.229(4) 1 d PG A 2 C12B C 0.0026(7) 0.388(3) 0.4344(5) 0.019(5) Uiso 0.229(4) 1 d PGU A 2 C13B C -0.1587(8) 0.511(3) 0.4077(6) 0.031(5) Uiso 0.229(4) 1 d PGU A 2 H13B H -0.2361 0.5168 0.4436 0.037 Uiso 0.229(4) 1 d PG A 2 C14B C -0.2075(9) 0.626(4) 0.3290(7) 0.028(6) Uiso 0.229(4) 1 d PGU A 2 H14B H -0.3177 0.7158 0.3121 0.033 Uiso 0.229(4) 1 d PG A 2 O1B O 0.3867(8) 0.254(3) 0.3568(3) 0.034(5) Uiso 0.229(4) 1 d PGU A 2 O2B O 0.6164(6) -0.002(2) 0.4649(3) 0.039(2) Uiso 0.229(4) 1 d PGU A 2 H2OB H 0.5757 0.0949 0.4206 0.059 Uiso 0.229(4) 1 d PG A 2 O3B O 0.7111(7) -0.2441(19) 0.6166(3) 0.039(2) Uiso 0.229(4) 1 d PGU A 2 H3OB H 0.7615 -0.2393 0.5774 0.059 Uiso 0.229(4) 1 d PG A 2 O4B O -0.0388(8) 0.288(3) 0.5675(5) 0.040(4) Uiso 0.229(4) 1 d PGU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(3) 0.015(2) 0.062(4) 0.004(2) -0.031(3) -0.004(2) C2 0.037(2) 0.014(2) 0.050(3) -0.0044(19) -0.0081(19) -0.005(2) C3 0.037(2) 0.016(2) 0.030(2) 0.0022(17) -0.005(2) -0.0041(19) C4 0.040(2) 0.023(3) 0.0312(19) -0.011(2) 0.010(3) -0.002(2) C5 0.0297(18) 0.013(2) 0.0260(17) -0.0038(17) -0.001(2) 0.0009(16) C6 0.048(3) 0.013(2) 0.027(2) -0.0096(18) 0.009(2) 0.002(2) C7 0.036(2) 0.018(2) 0.0217(16) -0.0036(17) -0.007(2) 0.0010(17) C8 0.0265(19) 0.027(3) 0.035(2) -0.0068(19) 0.004(2) -0.0013(18) C9 0.032(2) 0.024(3) 0.0313(17) -0.0024(18) 0.005(2) 0.0012(19) C10 0.039(2) 0.014(2) 0.0257(18) -0.0073(16) 0.012(2) -0.0042(18) C11 0.045(3) 0.020(3) 0.0227(18) -0.0034(16) 0.002(2) -0.004(2) C12 0.041(2) 0.010(2) 0.028(2) -0.0009(16) 0.004(2) -0.0107(19) C13 0.055(3) 0.016(2) 0.033(3) 0.0042(19) -0.0045(19) -0.014(3) C14 0.067(4) 0.0100(19) 0.043(3) 0.0056(19) -0.027(3) -0.010(2) O1 0.0392(17) 0.049(3) 0.0356(15) -0.0045(17) 0.0080(15) 0.0074(18) O2 0.0427(13) 0.0466(17) 0.0300(12) 0.0035(13) 0.0065(10) 0.0033(15) O3 0.0457(14) 0.0396(17) 0.0283(11) 0.0021(12) -0.0051(10) 0.0060(14) O4 0.051(2) 0.048(3) 0.0284(12) 0.0013(16) 0.0136(16) -0.0014(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(6) . ? C1 C14 1.386(8) . ? C1 H1 0.9500 . ? C2 C3 1.417(7) . ? C2 H2 0.9500 . ? C3 C12 1.386(8) . ? C3 C4 1.480(6) . ? C4 O1 1.245(8) . ? C4 C5 1.469(7) . ? C5 C6 1.405(5) . ? C5 C10 1.407(7) . ? C6 O2 1.347(5) . ? C6 C7 1.407(6) . ? C7 O3 1.342(5) . ? C7 C8 1.385(8) . ? C8 C9 1.376(6) . ? C8 H8 0.9500 . ? C9 C10 1.384(6) . ? C9 H9 0.9500 . ? C10 C11 1.463(7) . ? C11 O4 1.224(9) . ? C11 C12 1.485(7) . ? C12 C13 1.385(6) . ? C13 C14 1.383(8) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? O2 H2O 0.8400 . ? O3 H3O 0.8400 . ? C1B C2B 1.3830 . ? C1B C14B 1.3848 . ? C1B H1B 0.9500 . ? C2B C3B 1.4163 . ? C2B H2B 0.9500 . ? C3B C12B 1.3861 . ? C3B C4B 1.4805 . ? C4B O1B 1.2451 . ? C4B C5B 1.4696 . ? C5B C6B 1.4049 . ? C5B C10B 1.4070 . ? C6B O2B 1.3475 . ? C6B C7B 1.4067 . ? C7B O3B 1.3426 . ? C7B C8B 1.3851 . ? C8B C9B 1.3758 . ? C8B H8B 0.9500 . ? C9B C10B 1.3833 . ? C9B H9B 0.9500 . ? C10B C11B 1.4633 . ? C11B O4B 1.2248 . ? C11B C12B 1.4848 . ? C12B C13B 1.3849 . ? C13B C14B 1.3824 . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? O2B H2OB 0.8400 . ? O3B H3OB 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 119.1(5) . . ? C2 C1 H1 120.5 . . ? C14 C1 H1 120.5 . . ? C1 C2 C3 119.4(6) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C12 C3 C2 120.8(4) . . ? C12 C3 C4 122.0(5) . . ? C2 C3 C4 117.2(6) . . ? O1 C4 C5 121.7(4) . . ? O1 C4 C3 121.4(5) . . ? C5 C4 C3 117.0(6) . . ? C6 C5 C10 119.5(4) . . ? C6 C5 C4 118.8(5) . . ? C10 C5 C4 121.6(4) . . ? O2 C6 C5 122.6(4) . . ? O2 C6 C7 117.3(4) . . ? C5 C6 C7 120.1(5) . . ? O3 C7 C8 120.9(4) . . ? O3 C7 C6 119.8(5) . . ? C8 C7 C6 119.3(4) . . ? C9 C8 C7 120.2(5) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 121.9(6) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C5 118.9(4) . . ? C9 C10 C11 120.5(6) . . ? C5 C10 C11 120.7(4) . . ? O4 C11 C10 121.1(5) . . ? O4 C11 C12 120.7(4) . . ? C10 C11 C12 118.1(6) . . ? C13 C12 C3 118.9(5) . . ? C13 C12 C11 120.6(6) . . ? C3 C12 C11 120.5(5) . . ? C14 C13 C12 120.3(6) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C1 121.6(5) . . ? C13 C14 H14 119.2 . . ? C1 C14 H14 119.2 . . ? C2B C1B C14B 119.1 . . ? C2B C1B H1B 120.5 . . ? C14B C1B H1B 120.5 . . ? C1B C2B C3B 119.4 . . ? C1B C2B H2B 120.3 . . ? C3B C2B H2B 120.3 . . ? C12B C3B C2B 120.8 . . ? C12B C3B C4B 122.0 . . ? C2B C3B C4B 117.2 . . ? O1B C4B C5B 121.7 . . ? O1B C4B C3B 121.4 . . ? C5B C4B C3B 116.9 . . ? C6B C5B C10B 119.5 . . ? C6B C5B C4B 118.8 . . ? C10B C5B C4B 121.7 . . ? O2B C6B C5B 122.6 . . ? O2B C6B C7B 117.3 . . ? C5B C6B C7B 120.1 . . ? O3B C7B C8B 120.9 . . ? O3B C7B C6B 119.8 . . ? C8B C7B C6B 119.4 . . ? C9B C8B C7B 120.2 . . ? C9B C8B H8B 119.9 . . ? C7B C8B H8B 119.9 . . ? C8B C9B C10B 121.9 . . ? C8B C9B H9B 119.0 . . ? C10B C9B H9B 119.0 . . ? C9B C10B C5B 118.8 . . ? C9B C10B C11B 120.5 . . ? C5B C10B C11B 120.6 . . ? O4B C11B C10B 121.1 . . ? O4B C11B C12B 120.7 . . ? C10B C11B C12B 118.2 . . ? C13B C12B C3B 118.8 . . ? C13B C12B C11B 120.6 . . ? C3B C12B C11B 120.5 . . ? C14B C13B C12B 120.3 . . ? C14B C13B H13B 119.8 . . ? C12B C13B H13B 119.8 . . ? C13B C14B C1B 121.5 . . ? C13B C14B H14B 119.3 . . ? C1B C14B H14B 119.3 . . ? C6B O2B H2OB 109.5 . . ? C7B O3B H3OB 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 1.3(7) . . . . ? C1 C2 C3 C12 -0.9(6) . . . . ? C1 C2 C3 C4 -178.4(4) . . . . ? C12 C3 C4 O1 -178.6(4) . . . . ? C2 C3 C4 O1 -1.1(5) . . . . ? C12 C3 C4 C5 2.9(5) . . . . ? C2 C3 C4 C5 -179.6(4) . . . . ? O1 C4 C5 C6 -0.4(5) . . . . ? C3 C4 C5 C6 178.1(3) . . . . ? O1 C4 C5 C10 179.4(3) . . . . ? C3 C4 C5 C10 -2.1(5) . . . . ? C10 C5 C6 O2 -179.5(4) . . . . ? C4 C5 C6 O2 0.3(6) . . . . ? C10 C5 C6 C7 2.0(5) . . . . ? C4 C5 C6 C7 -178.1(3) . . . . ? O2 C6 C7 O3 0.4(6) . . . . ? C5 C6 C7 O3 179.0(4) . . . . ? O2 C6 C7 C8 179.3(4) . . . . ? C5 C6 C7 C8 -2.1(6) . . . . ? O3 C7 C8 C9 179.4(4) . . . . ? C6 C7 C8 C9 0.5(6) . . . . ? C7 C8 C9 C10 1.2(6) . . . . ? C8 C9 C10 C5 -1.3(6) . . . . ? C8 C9 C10 C11 179.1(3) . . . . ? C6 C5 C10 C9 -0.3(5) . . . . ? C4 C5 C10 C9 179.9(3) . . . . ? C6 C5 C10 C11 179.3(3) . . . . ? C4 C5 C10 C11 -0.6(5) . . . . ? C9 C10 C11 O4 1.0(5) . . . . ? C5 C10 C11 O4 -178.6(3) . . . . ? C9 C10 C11 C12 -177.9(4) . . . . ? C5 C10 C11 C12 2.5(5) . . . . ? C2 C3 C12 C13 0.8(7) . . . . ? C4 C3 C12 C13 178.2(4) . . . . ? C2 C3 C12 C11 -178.4(3) . . . . ? C4 C3 C12 C11 -1.0(6) . . . . ? O4 C11 C12 C13 0.2(6) . . . . ? C10 C11 C12 C13 179.1(4) . . . . ? O4 C11 C12 C3 179.3(4) . . . . ? C10 C11 C12 C3 -1.8(6) . . . . ? C3 C12 C13 C14 -1.1(8) . . . . ? C11 C12 C13 C14 178.0(5) . . . . ? C12 C13 C14 C1 1.6(9) . . . . ? C2 C1 C14 C13 -1.7(9) . . . . ? C14B C1B C2B C3B 1.3 . . . . ? C1B C2B C3B C12B -0.9 . . . . ? C1B C2B C3B C4B -178.4 . . . . ? C12B C3B C4B O1B -178.6 . . . . ? C2B C3B C4B O1B -1.1 . . . . ? C12B C3B C4B C5B 2.9 . . . . ? C2B C3B C4B C5B -179.7 . . . . ? O1B C4B C5B C6B -0.5 . . . . ? C3B C4B C5B C6B 178.1 . . . . ? O1B C4B C5B C10B 179.4 . . . . ? C3B C4B C5B C10B -2.1 . . . . ? C10B C5B C6B O2B -179.5 . . . . ? C4B C5B C6B O2B 0.4 . . . . ? C10B C5B C6B C7B 2.0 . . . . ? C4B C5B C6B C7B -178.1 . . . . ? O2B C6B C7B O3B 0.4 . . . . ? C5B C6B C7B O3B 179.0 . . . . ? O2B C6B C7B C8B 179.3 . . . . ? C5B C6B C7B C8B -2.1 . . . . ? O3B C7B C8B C9B 179.4 . . . . ? C6B C7B C8B C9B 0.5 . . . . ? C7B C8B C9B C10B 1.2 . . . . ? C8B C9B C10B C5B -1.3 . . . . ? C8B C9B C10B C11B 179.1 . . . . ? C6B C5B C10B C9B -0.3 . . . . ? C4B C5B C10B C9B 179.8 . . . . ? C6B C5B C10B C11B 179.3 . . . . ? C4B C5B C10B C11B -0.6 . . . . ? C9B C10B C11B O4B 1.0 . . . . ? C5B C10B C11B O4B -178.6 . . . . ? C9B C10B C11B C12B -177.9 . . . . ? C5B C10B C11B C12B 2.5 . . . . ? C2B C3B C12B C13B 0.8 . . . . ? C4B C3B C12B C13B 178.2 . . . . ? C2B C3B C12B C11B -178.4 . . . . ? C4B C3B C12B C11B -1.0 . . . . ? O4B C11B C12B C13B 0.2 . . . . ? C10B C11B C12B C13B 179.1 . . . . ? O4B C11B C12B C3B 179.3 . . . . ? C10B C11B C12B C3B -1.8 . . . . ? C3B C12B C13B C14B -1.1 . . . . ? C11B C12B C13B C14B 178.0 . . . . ? C12B C13B C14B C1B 1.6 . . . . ? C2B C1B C14B C13B -1.7 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.84 1.81 2.546(4) 145.5 . O3 H3O O2 0.84 2.23 2.691(4) 114.9 . O3 H3O O4 0.84 1.99 2.712(6) 143.3 2 O2B H2OB O1B 0.84 1.81 2.546 145.5 . O3B H3OB O2B 0.84 2.23 2.691 114.9 . O3B H3OB O4B 0.84 2.42 2.907 118.0 1_645 O3B H3OB O4B 0.84 2.57 3.054 118.2 1_655 O3 H3O O1B 0.84 2.29 3.023(7) 146.3 2 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.188 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.048